Silaborative assembly of allenamides and alkynes: highly regio- and stereocontrolled access to bi- or trimetallic skipped dienes

Pradhan, Tapas R., Paudel, Mukti, Feoktistova, Taisiia, Cheong, Paul Ha?Yeon and Park, Jin Kyoon 2022. Silaborative assembly of allenamides and alkynes: highly regio- and stereocontrolled access to bi- or trimetallic skipped dienes. Angewandte Chemie 134 (17) , e202116154. 10.1002/ange.202116154

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Abstract

A highly stereo- and regiocontrolled multicomponent approach to skipped 1,4-dienes decorated with one boryl and two silyl functionalities is described. This Pd-catalyzed atom-economical union of allenamides, alkynes, and Me2PhSiBpin (or Et3SiBpin) proceeds without the use of phosphine ligands, instead relying on chelation through the internal amide group of the allenamide sulfonyl. A variety of alkynes, including those derived from complex bioactive molecules, can be efficiently coupled with allenamides and Me2PhSiBpin in good yields and with excellent selectivity. The synthetic potential was demonstrated through multiple valuable chemoselective transformations, establishing new disconnections for functionalized dienes. Density functional theory calculations revealed that the reaction first proceeded through borylation of the allenamide, followed by silylation of the alkyne and then reductive elimination, which convergently assemble the skipped 1,4-diene.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	0044-8249
Date of Acceptance:	9 February 2022
Last Modified:	25 Mar 2024 10:13
URI:	https://orca.cardiff.ac.uk/id/eprint/165574

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